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Whit Stillman did not get the memo.

Or rather, he got it, scanned it with a frown, shoved it into the pocket of his J. Press khakis, and continued on his way, whistling a jaunty old tune (now at a slightly higher volume). The crumpled-up memorandum, widely circulated among American artists, includes the following:

1. Harvard students and other children of privilege are entitled, narcissistic wastrels.

Stillman has spent his filmmaking career roguishly flouting these (actually unwritten) rules, and some others. His artful defiance has yielded a small but wonderful oeuvre comprising four films, all of which he wrote and directed: Metropolitan (1990), Barcelona (1994), The Last Days of Disco (1998), and now Damsels in Distress. Each of Stillman’s films follows a different group of privileged, highly educated, hyper-articulate young people just emerging from the chrysalis of adolescence. Their naked, earnest search for moral truth is oddly, delightfully interspersed with bouts of rich sensual indulgence. This combination is key to Stillman’s art: He is a nostalgist and an amateur moralist; but still, through it all, an exuberant, unembarrassed partisan of joie de vivre optimism.

More by Ian Marcus Corbin

Stillman’s focus on the American upper class, a group one of his characters terms the“Urban Haute Bourgeoisie” or “UHB,” has been the easy headline of his career. Stillman has been frequently called “the WASP Woody Allen,” and his first three films are sometimes called the “Yuppie Trilogy.” Some have recoiled at this focus, charging Stillman with snobbery (see rule one above). Evelyn Waugh, one of Stillman’s favorite novelists, tended to write about the English upper classes and answered similar criticism with a perennially sound rebuttal: “I reserve the right to deal with the kind of people I know best.” Stillman’s impeccably WASP lineage and Harvard education are reason enough to justify his focus on the UHB, but this focus also fills a gap in American art and life.

In his classic essay “Manners, Morals, and the Novel,” the great Jewish literary critic Lionel Trilling (another of Stillman’s favorite writers) wrote that most American novelists shared a crippling blind spot. They wanted to understand American society, but they could not reflect with any honesty on American manners because to do so would require engagement with the different manners of the different social classes, and in our theoretically horizontal society, there are no such differences. Or if there are, they are the result of showy affectation, and so a good egalitarian conscience requires that the manners of the upper classes be mocked and those of the lower classes bowdlerized and valorized.

Which is to say, neither of them can be honestly examined. Trilling argues that this failure is devastating for art that seeks to depict social realities because manners are a chief way in which a group’s values are embodied in day-to-day actions.

This blind spot is also bad for America’s self-understanding. We have not had a president without an Ivy League degree since 1989, and we won’t have another until at least 2017. Every one of our sitting Supreme Court justices went either to Harvard or Yale. East Coast elites really do run much of the country, and yet they serve as perpetual whipping boys for sanctimonious artists and Manichean populists on the left and right.

The upshot is that the milieu of our leaders remains woefully underexamined. There is much talk of a growing disconnect between upper and lower in America, and the artistic failure Trilling describes is not helping. Whit Stillman is one of the rare contemporary artists willing to deal sympathetically (if also critically and lightheartedly) with our untitled aristocracy. His humanization of an often-vilified demographic is an artistic virtue and, perhaps, a social service.